Inhibitor of autotaxin, antagonist of LPA1 and LPA3
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Oleoyl 3-carbacyclic Phosphatidic Acid

Item No. 10010299

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(9Z)-9-octadecenoic acid, (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester
CAS Number
779333-58-3
Synonyms
  • 3-ccPA 18:1
Molecular Formula
C22H41O5P
Formula Weight
416.5
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in chloroform
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 5 mg/ml
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)OCC1CCP(=O)(O)O1
InChi Code
InChI=1S/C22H41O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(23)26-20-21-18-19-28(24,25)27-21/h9-10,21H,2-8,11-20H2,1H3,(H,24,25)/b10-9-
InChi Key
IJSTZKWSILWQEC-KTKRTIGZSA-N
Side Chain Carbon Sum
18:1
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $86

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    1 mg

    $163

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    5 mg

    $687

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    10 mg

    $1,202

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    Product Description

    Cyclic phosphatidic acids (cPAs) are naturally occurring analogs of lysophosphatidic acid (LPA) in which the sn-2 hydroxy group forms a 5-membered ring with the sn-3 phosphate.1,2 Carba-derivatives of cPA (ccPA) are modified at the sn-2 (2-ccPA) or sn-3 (3-ccPA) linkage, preventing the opening of cPA to produce lysophosphatidic acid (LPA).3 Oleoyl 3-Carbacyclic Phosphatidic Acid (3-ccPA 18:1) is a cyclic LPA analog that contains the 18:1 fatty acid, oleate, at the sn-1 position of the glycerol backbone.3 At 25 μM, it inhibits the transcellular migration of MM1 cells across mesothelial cell monolayers in response to fetal bovine serum (90.1%) or LPA (99.9%) without affecting proliferation.3 3-ccPA 18:1, at 0.1-1.0 μM, significantly inhibits autotaxin,4,5 an enzyme that is important in cancer cell survival, growth, migration, invasion, and metastasis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kobayashi, T., Tanaka-Ishii, R., Taguchi, R., et al. Existence of a bioactive lipid, cyclic phosphatidic acid, bound to human serum albumin. Life Sci. 65(21), 2185-2191 (1999).

    2. Mukai, M., Imamura, F., Ayaki, M., et al. Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA). Int. J. Cancer 81(6), 918-922 (1999).

    3. Uchiyama, A., Mukai, M., Fujiwara, Y., et al. Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid. Biochim. Biophys. Acta 1771(1), 103-112 (2007).

    4. Baker, D.L., Fujiwara, Y., Pigg, K.R., et al. Carba analogs of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis. The Journal of Biological Chemisty 281(32), 22786-22793 (2006).

    5. Prestwich, G.D., Gajewiak, J., Zhang, H., et al. Phosphatase-resistant analogues of lysophosphatidic acid: Agonists promote healing, antagonists and autotaxin inhibitors treat cancer. Biochim. Biophys. Acta 1781, 588-594 (2008).